Hydroxylamine compounds are very important compounds as intermediate products for, for example, polymerization inhibitors, antioxidants, agricultural chemicals, medicines, cosmetics and electronic industrial chemicals.
Phenylhydroxylamine as an example of the hydroxylamine compound is a useful compound as an intermediate product for polymerization inhibitors and antioxidants, and had been conventionally manufactured by a method where nitrobenzene is reduced with sodium hydrosulfide or a method where nitrobenzene is reacted with hydrogen using a platinum-carbon catalyst (see, U.S. Pat. No. 3,694,509).
However, in the former method, yield of an objective product is not high enough to be practically used due to a low selectivity of the reaction, and there is fear that offensive odor of sodium hydrosulfide to be used affect working environment.
On the other hand, in the latter method, yield of an objective product is not high enough to be commercially used similarly to the former method, and there is a problem that elevation of reaction temperature to improve the yield results in, on the contrary, lowering of the yield due to decrease of reaction selectivity. Further, in the latter method, not only formation ratio of aniline as a byproduct is high but also platinum-carbon to be used as a reaction catalyst requires special attention in handling because of a combustible substance. Still further, recovery and reuse of the above platinum catalyst after use requires extremely complicated procedures due to a very small particle size.
Under the above circumstances, development of a method for manufacturing (producing) a hydroxylamine compound efficiently, industrially and safely is demanded.